7719-09-7

Basic information

• Product Name: Thionyl chloride
• Synonyms: chloruredethionyle;SOCl2;Sulfinyl chloride;Sulfinyl dichloride;sulfinylchloride;Sulfoxidechloride;Sulfur chloride oxide;Sulfur chloride oxide (Cl2SO)
• CAS NO: 7719-09-7
• Molecular Formula: Cl₂OS
• Molecular Weight: 118.97
• EINECS: 231-748-8
• Product Categories: Inorganics;Chlorination;Halogenation;Synthetic Organic Chemistry;Reagent Grade;Electrolytes;C-X Bond Formation (Halogen);Synthetic Reagents;ChlorinationMaterials Science;ElectrolytesEssential Chemicals;Alternative Energy;Reagent Plus;Routine Reagents;C-X Bond Formation (Halogen);Alternative Energy;Chemical Synthesis;Materials Science;Organic Solvents;Synthetic Reagents;Essential Chemicals;Inorganic Salts;Reagent Plus;Research Essentials;Solutions and Reagents;Reagent Grade
• Mol File: 7719-09-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: -105 °C
• Boiling Point: 79 °C(lit.)
• Flash Point: 105°C
• Appearance: ≤50(APHA)/Liquid
• Density: 1.64 g/mL at 20 °C
• Vapor Density: 4.1 (vs air)
• Vapor Pressure: 97 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.518(lit.)
• Storage Temp.: Store at RT.
• Solubility: Miscible with toluene, chloroform, benzene, carbon tetrachloride
• Water Solubility: REACTS
• Sensitive: Moisture Sensitive
• Stability: Reacts violently with water. Incompatible with most common metals, strong reducing agents, strong bases, alcohols, amines.
• Merck: 14,9348
• CAS DataBase Reference: Thionyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Thionyl chloride(7719-09-7)
• EPA Substance Registry System: Thionyl chloride(7719-09-7)

Safety Data

• Hazard Codes: C
• Statements: 14-20/22-29-35-40-34-20/21/22
• Safety Statements: 26-36/37/39-45-28-27
• RIDADR: UN 1836 8/PG 1
• WGK Germany: 1
• RTECS: XM5150000
• F: 19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: I
• Hazardous Substances Data: 7719-09-7(Hazardous Substances Data)

Usage

Chemical Description

Different sources of media describe the Chemical Description of 7719-09-7 differently. You can refer to the following data:
1. Thionyl chloride is a colorless to yellowish liquid that is used as a chlorinating agent.
2. Thionyl chloride is a reactive chemical used as a chlorinating agent.
3. Thionyl chloride is an inorganic compound used as a chlorinating agent.
4. Thionyl chloride is used to convert the acids into ethyl esters.
5. Thionyl chloride is used to generate the acid chloride for the amidation step, and mCPBA is used to oxidize the acylanilide to the sulfone.
6. Thionyl chloride is used for the synthesis of 1,1'-sulfinylditriazole.
7. Thionyl chloride is used to convert the carboxylic acids into acid chlorides.

Outline

Thionyl chloride, at room temperature and pressure, is a colorless or pale yellow liquid with a pungent odor. It has a relative density of 1.676, melting point of-104.5 ℃ and the boiling point of 78.8 ℃. Upon coming across water, it is easily decomposed into sulfur dioxide and hydrogen chloride. It is soluble in benzene, chloroform and carbon tetrachloride. It begins to decompose upon being heated to 150 °C with complete decomposition at 500°C. Thionyl chloride sometimes can be easily confused with thionyl chlorine (SO2Cl2). However, these two compounds actually have a large difference in their chemical nature with its chlorine atom having a strong substitution capacity on hydroxyl group or sulfur group. Thionyl chloride can form corresponding chlorides with hydroxyl-containing phenol or hydroxyl-containing alcohol to form the corresponding chlorides; it can have reaction with Grignard reagent to generate the corresponding sulfoxide compound. The molecular structure of thionyl chloride is cone type wherein the sulfur (VI) center contains one lone pair of electrons. However, COCl2 has planar configuration. Owing to the strong reaction between the thionyl chloride and water, SOCl2 does not exist in nature.

Purification

Thionyl chloride crude product often contains impurities including sulfuryl chloride, sulfur monochloride and sulfur dichloride. In order to obtain a higher purity of thionyl chloride, sulfur powder has to be added for refluxing and distillation to obtain high-purity chloride sulfoxide. The detailed mechanisms of reactions remain to be unclear. According to my analysis, it may be that it can prevent the thionyl chloride being decomposed into sulfur dichloride, sulfur dioxide and chlorine during the process of distillation. The detailed purification method is that: put together of 450 ml of thionyl chloride with 12.5g of sulfur powder for being heated under reflux for 4.5 hours, followed by efficient fractionating column for twice to obtain pure colorless. Alternatively, you can also apply distillation purification in the presence of triphenyl phosphite. The removed impurities should be sulfuryl chloride, sulfur monochloride and sulfur dichloride.

Uses

Different sources of media describe the Uses of 7719-09-7 differently. You can refer to the following data:
1. Thionyl chloride is an important intermediate of organic chemistry and is mainly used in medicine, pesticides, dyes and industrial organic synthesis industry as chlorinating agent. Consumption structure: the pharmaceutical industry accounted for 25%, pesticide industry accounted for 50%, dyestuff industry accounted for 5% and other industries accounted for 20%. The pesticide industry contributes the major part for consumption of thionyl chloride and is mainly used for the production of inabenfide, valerate, fenvalerate, mosquito-killing dimerthrin, flucythrinate, diflubenzuron, isocarbophos, fenpropathrin, endosulfan, deltamethrin, a (b) group chlorpyrifos, oxazolidinone, quizalofop and warfarin. Because thionyl chloride can have fierce reaction with water, it is able to have reaction with metal chloride hydrated salt for production with anhydrous metal chlorides. MCln ? xH2O + x SOCl2 → MCln + x SO2 + 2x HCl Thionyl chloride was subjected heating reflux with a transition metal oxide and can further generate the corresponding oxychloride of the metal: WO3 + 2SOCl2 → WOCl4 + 2SO2 Thionyl chloride has been widely used for converting alcohol and the carboxylic acid into the corresponding acid chloride and chlorinated hydrocarbons. Compared with other agents (such as phosphorus penta-chloride), thionyl chloride is often the preferred reagents, because both the reaction product of sulfur dioxide and hydrogen chloride are gaseous and is easily to be separated. The excess amount of thionyl chloride can be removed by distillation. RC (= O)-OH + O = SCl2 → RC (= O)-Cl + SO2 + HCl R-OH + O = SCl2 → R-Cl + SO2 + HCl. Sulfoacid can react with thionyl chloride to generate sulfonyl chloride. Sulfinic acid can have reaction with thionyl chloride to generate sulfinyl chloride. Phosphonic acid can have reaction with thionyl chloride to generate phosphine chloride. Thionyl chloride can react with mono-substituted formamide to generate the corresponding isonitriles. Amide can react with thionyl chloride to generate imine acyl chloride. Primary amide, upon co-heating with thionyl chloride, will be further dehydrated to become nitrile. The above information is edited by the lookchem of Dai Xiongfeng.
2. It can be applied to medicine, pesticide and dye industries and mainly used for the production of isocarbophos, sumicidin, propargite tetramisole hydrochloride, indomethacin, and vitamin A, etc. It can be used as the chlorinating agents for organic synthesis such as chlorination of alcoholic hydroxyl group, chlorination of carboxylic acid, chlorination of acid anhydride and the chlorine displacement of organic sulfonic acid or carboxylic acid. It can also be used for making acyl chloride as well as being used for the manufacture of pharmaceutical intermediates such as tetramisole hydrochloride and synthomycin palmitate. It can also be used as a dehydrating agent or solvent.
3. In the manufacture of lithium batteries; in the synthesis of herbicides, surfactants, drugs, vitamins, and dyestuffs.
4. For making acyl chlorides, to replace OH or SH groups with chlorine atoms; reacts with Grignard reagents to form the corresponding sulfoxides. Review of use in organic synthesis: J. S. Pizey, Synthetic Reagents vol. 1 (John Wiley, New York, 1974) pp 321-357.
5. Thionyl chloride (SOCl2) is used as a chlorinating agent in manufacturing organic compounds. It is also used as a solvent in high-energy lithium batteries.

Synthesis method

Currently there are major approaches for industrial production of thionyl chloride including chlorosulfonic acid method, sulfur dioxide gas-phase method and phosphorus oxychloride cogeneration. Fixed consumption amount: Production methods raw material and specifications consumption quota/t ? t-1 Chlorosulfonic acid method chlorosulfonic acid (95%) 1.1 Liquid chlorine (99%) 0.91 Sulfur powder (99.5%) 0.42 Fumed sulfur dioxide (99.5%) 0.22 Liquid chlorine (99%) 0.88 Sulfur dioxide (99%) 0.44 Cogeneration phosphorus oxychloride, phosphorus trichloride (98%) 1.3 Liquid chlorine (99%) 0.66 Sulfur dioxide (99%) 0.64

Toxicity

Thionyl chloride is toxic and is corrosive and has tearing property. Pathways: inhaled, ingested, percutaneous absorption. Health hazard: inhalation, oral administration or percutaneous absorption is harmful to our health. The eyes, skin, mucosa and respiratory tract have a strong stimulating effect and can cause burn wound. After inhalation, it may be lethal due to causing the spasm and dropsy of throat and bronchial. Poisoning performance includes burning sensation, coughing, wheezing, and dizziness, and laryngitis, shortness of breath, headache, nausea and vomiting. Acute toxicity: LC50: 2435 mg/m3 (rat inhalation) Irritation: a rabbit eyes: 1380 μg, severe stimulation. Protective: This product can burn the skin and is irritable to the mucous membrane. During operation, the worker should wear protective equipment and should wash immediately with plenty of water if being splashed on skin. First-aid Skin contact: Immediately remove contaminated clothing, rinse with plenty of water for at least 15 minutes. Then go for medical treatment. Eye contact: immediately lift up eyelid; wash with large flows of water or saline thoroughly for at least 15 minutes. Then go for medical treatment. Inhalation: rapidly leave the scene to place with fresh air. Keep the airway open. If breathing is difficult, give oxygen. If breathing stops, immediately apply artificial respiration and send for medical treatment. Ingestion: for misusage people, immediately rinse the mouth with water and drink milk or egg white. Then go for medical treatment.

How to deal with the wasted thionyl chloride so that the environment is not affected

It is recommended for distillation recycling. If you want to deal with it, you can add it slowly into ice water for decomposition into SO2 and HCL which are subject to further treatment. If the amount of the wasted thionyl chloride is large, you can consider recycle or sold outside for treatment. If the amount is small, you can add it drop wise into the alkaline water for decomposition and neutralization.

Packing and storage

Packaging: glass or plastic barrels (tank) full open drums; glass or plastic bucket (cans); outside: the ordinary wooden box or wooden grille half; frosted glass bottles or threaded glass; outside: the ordinary wooden box; ampoules; outside: ordinary wooden box. Storage precautions: for railway transport, it should be subject to package strictly in accordance with the dangerous cargo form in the <> (Ministry of railway of china). Upon the shipment, the packaging should be complete and the loading should be safe. During the process of transport, we should ensure that the container does not leak, does not fall off and does not been broken. It is not allowed to mix it with alkali or edible chemicals for operation and transport. During the transport, the transport vehicles should be equipped with spill response equipment. During the transport process, we should prevent sunshine exposure, rain and high temperature. During the road transport, the vehicles should be driven according to the provided routes with no stopping in residential areas and densely populated areas. It should be stored in a cool, ventilated warehouse with the storage temperature being not exceed 25 ℃ and the relative humidity being less than 75%. Keep the container closed. Moreover, we should store it separately from bases and avoid mixing for storage. Storage areas should be equipped with spill response equipment and suitable host materials.

Chemical Properties

Different sources of media describe the Chemical Properties of 7719-09-7 differently. You can refer to the following data:
1. It is colorless or light yellow volatile liquid with a strong suffocating odor. It can also be miscible with benzene, chloroform and carbon tetrachloride.
2. Thionyl chloride is a pale yellow to reddish liquid. Suffocating odor like sulfur dioxide. Fumes form when exposed to moist air.

Production method

It can be produced with the reaction between sulfur trioxide and sulfur dichloride. Chlorosulfonic acid method: first add sulfur powder to the reactor, put through the chlorine gas for reaction to generate sulfur monochloride. Then add a certain amount of chlorine acid and sulfur monochloride to the reactor; put through chlorine gas at below 50 ℃ for reaction; the resulted mixture was further subject to the crude distillation and condensation; further collect the material liquid below 130 ℃ and feed to the distillation pot; in order to make the low-boiling sulfur dichloride be convert to sulfur chloride for further being left in the pot, then you have to add 15% to 20% the amount of the crude product of sulfur and then send for distillation; reflux for 4h until giving normal color; collect the fraction between 75-80 ℃ to obtain the finished product. The reaction equation is: 2ClSO3H + S2C12 + C12 → 2SOC12 + 2SO2 + 2HCl Sulfur dioxide method: take sulfur, liquid chlorine and liquid sulfur dioxide as raw material; apply whole-cycle and liquid circulation method for production of high-purity alumina thionyl chloride with a purity of 99%; this method has advanced technology, high product quality and releases less "three wastes".

Professional standards

TWA 1 PPM (5 mg/cubic meter); STEL 1 PPM (5 mg/m3)

Physical properties

Pale yellow to red fuming liquid; suffocating odor; refractive index 1.517 at 20°C; density 1.631 g/mL at 20°C; freezes at -101°C; boils at 75.6°C; decomposes at 140°C; decomposes in water; soluble in benzene, chloroform, and carbon tetrachloride.

Definition

ChEBI: Thionyl chloride is a sulfinyl halide in which both of the halide atoms are chorines. It is a sulfinyl halide and a chlorine molecular entity.

Preparation

Sulfurous oxychloride can be prepared by oxidation of sulfur dichloride with sulfur trioxide: SCl2 + SO3 → SOCl2 + SO2 Also, the compound can be prepared by reacting sulfur dioxide with phosphorus pentachloride: SO2 + PCl5 → SOCl2 + POCl3.

General Description

Thionyl chloride appears as a colorless to yellow fuming liquid with a suffocating pungent odor. Boiling point 79 °C. A lachrymator. Highly corrosive and toxic. Long-term inhalation of low concentrations or short-term inhalation of high concentrations has adverse health effects.

Reactivity Profile

Thionyl chloride reacts, potentially explosively, with dimethyl sulfoxide or dimethylformamide containing traces of iron or zinc [Spitulnik, M. J., Chem. Eng. News, 1977, 55(31), p. 31]. Undergoes violent reactions with bases (ammonia, sodium hydroxide, potassium hydroxide, amines), alkali metals (sodium, potassium), esters (ethyl acetate), toluene mixed with ethanol / water [Bretherick, 5th ed., 1995, p. 1325]. Has an expansion ratio from gas to liquid of nearly 1000:1. Hence may cause an explosion if heated while contained [MCA Case History No. 1808]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Perchloric acid ignites on contact with sulfinyl chloride. (Bailar, 1973, Vol. 2, 1442). SOCl2 reacts with esters, such as ethyl acetate, forming toxic SO2 gas and water soluble/toxic acyl chlorides, catalyzed by Fe or Zn (Spagnuolo, C.J. et al. 1992. Chemical and Engineering News 70(22):2.).

Hazard

Strong irritant to skin, tissue, and upper respiratory tract.

Health Hazard

CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by inhalation. The material itself is more toxic than sulfur dioxide. Has a pungent odor similar to that of sulfur dioxide; it fumes upon exposure to air. Violent reaction with water releases hydrogen chloride and sulfur dioxide. Both these decomposition products constitute serious toxicity hazards. A corrosive irritant that causes burns to the skin and eyes. A powerful chlorinating agent. Potentially explosive reaction with ammonia, bis(dimethy1amino)sulfoxide - (above 80℃), chloryl perchlorate, 1,2,3- cyclohexanetrione trioxime + sulfur dioxide, dimethyl sulfoxide, hexafluoroisopropylideneaminolithium. Violent reaction or ignition with 2,4-hexadiyn-1-6-di01, onitrobenzoyl acetic acid, o-nitrophenylacetic acid, sodum (ignites at 300℃). Incompatible with ammonia, dimethyl formamide + trace iron or zinc, linseed oil + quinoline, toluene + ethanol + water. When heated to decomposition it emits toxic fumes of SOx and Cl-. See also HYDROGEN CHLORIDE and SULFUR DIOXIDE.

Potential Exposure

Thionyl chloride is used as specialty chlorinating agent, particularly in preparation of organic acid chlorides; in organic synthesis; as a catalyst.

Shipping

UN1836 Thionyl chloride, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Crude SOCl2 can be freed from sulfuryl chloride, sulfur monochloride and sulfur dichloride by refluxing it with sulfur and then fractionally distilling twice. [The SOCl2 is converted to SO2 and sulfur chlorides. The S2Cl2 (b 135.6o) is left in the residue, whereas SCl2 (b 59o) passes over in the forerun.] The usual purification is to distil it from quinoline (50g SOCl2 to 10g quinoline) to remove acid impurities, followed by distillation from boiled linseed oil (50g SOCl2 to 20g of oil). Precautions must be taken to exclude moisture. Thionyl chloride is used extensively in organic syntheses and can be prepared by distillation of technical SOCl2 in the presence of diterpene (12g/250mL SOCl2), and avoiding overheating. Further purification is achieved by redistillation from linseed oil (1-2%) [Rigby Chem Ind (London) 1508 1969]. Gas chromatographically pure material is obtained by distillation from 10% (w/w) triphenyl phosphite [Friedman & Wetter J Chem Soc (A) 36 1967, Larsen et al. J Am Chem Soc 108 6950 1986]. HARMFUL VAPOURS.

Incompatibilities

Reacts violently with water releasing sulfur dioxide and hydrogen chloride. Keep away from water, acids, alcohols, alkalis, ammonia, chloryl perchlorate.

Waste Disposal

Spray on a thick layer of a (1:1) mixture of dry soda ash and slaked lime behind a shield. After mixing, spray water from an atomizer with great precaution. Transfer slowly into a large amount of water. Neutralize and drain into the sewer with sufficient water.

InChI:InChI=1/Cl2OS/c1-4(2)3

Synthetic route

sulfur dichloride (10545-99-0) + sulfur trioxide (7446-11-9) → thionyl chloride (7719-09-7) + sulfur dioxide (7446-09-5)

Conditions	Yield
In neat (no solvent) below -10°C or under pressure;;	A 100% B n/a

hydrogenchloride (7647-01-0) + N-phenylsulfinylamine (222851-56-1) → thionyl chloride (7719-09-7) + aniline hydrochloride (142-04-1)

Conditions	Yield
In Petroleum ether decompn. of thioaniline dissolved in dild. petroleum (b.p. 200-250°C) on introduction of dry HCl (shaking) at -10°C;; filtration (anilinium chloride); fractionation;;	A 94% B n/a

sulfur dichloride (10545-99-0) + sulfur trioxide (7446-11-9) → thionyl chloride (7719-09-7) + pyrosulfuryl chloride (7791-27-7) + sulfur dioxide (7446-09-5)

Conditions	Yield
In neat (no solvent) SO3 is distilled (from 65 % oleum) into cooled (ice/water) vessel containing SCl2; evolution of SO2;; multiple fractionation (at last in presence of sulfur);;	A 80% B n/a C n/a

tetrachloromethane (56-23-5) → phosgene (75-44-5) + thionyl chloride (7719-09-7)

Conditions	Yield
With sulfur dioxide In neat (no solvent) reaction of CCl4 with SO2 on heating to 200°C;;	A n/a B 72%

Ethanesulfonyl chloride (594-44-5) → thionyl chloride (7719-09-7) + chloroethane (75-00-3) + phosphorus pentachloride (10026-13-8, 874483-75-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8)

phosphorus pentachloride (10026-13-8, 874483-75-7) + benzenesulfonyl chloride (98-09-9) → thionyl chloride (7719-09-7) + chlorobenzene (108-90-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8)

Conditions	Yield
at 200 - 210℃;

tetrachloromethane (56-23-5) + aluminium trichloride (7446-70-0) + SO2 → thionyl chloride (7719-09-7)

Conditions	Yield
at 200℃; unter Druck;

carbon disulfide (75-15-0) + hypochlorous acid anhydride → phosgene (75-44-5) + thionyl chloride (7719-09-7)

phosgene (75-44-5) + SO2 → thionyl chloride (7719-09-7) + carbon dioxide (124-38-9) + sulfur chloride

Conditions	Yield
at 200 - 400℃;

Trichloromethanesulfonyl chloride (2547-61-7) → tetrachloromethane (56-23-5) + phosgene (75-44-5) + thionyl chloride (7719-09-7) + sulfur dioxide

Conditions	Yield
at 200℃;

aluminium trichloride (7446-70-0) + chloroform (67-66-3) + SO2 → thionyl chloride (7719-09-7)

Conditions	Yield
at 150℃;

diethyl sulphite (623-81-4) + phosphorus pentachloride (10026-13-8, 874483-75-7) → thionyl chloride (7719-09-7) + ethyl chlorosulfite (6378-11-6) + chloroethane (75-00-3)

Conditions	Yield
bei niedrigerer Temperatur;

dipropyl sulfite (623-98-3) + phosphorus pentachloride (10026-13-8, 874483-75-7) → thionyl chloride (7719-09-7) + 1-Chloropropane (540-54-5)

Conditions	Yield
beim Erwaermen;

sulfurous acid dibutyl ester (626-85-7) + phosphorus pentachloride (10026-13-8, 874483-75-7) → thionyl chloride (7719-09-7) + n-Butyl chloride (109-69-3)

Conditions	Yield
bei schwachem Erwaermen;

aluminium trichloride (7446-70-0) + sulfuryl dichloride (7791-25-5) + 1,2,4,5-tetrachlorobenzene (95-94-3) + disulfur dichloride → tetrachloromethane (56-23-5) + thionyl chloride (7719-09-7) + pentachlorobenzene (608-93-5) + hexachlorobenzene (118-74-1)

ethyl chlorosulfite (6378-11-6) + phosphorus pentachloride (10026-13-8, 874483-75-7) → thionyl chloride (7719-09-7) + chloroethane (75-00-3) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8)

Conditions	Yield
at 25℃;

p-hydoroxybenzenesulfonic acid (98-67-9) + phosphorus pentachloride (10026-13-8, 874483-75-7) → thionyl chloride (7719-09-7) + para-dichlorobenzene (106-46-7) + 4-chlorophenylphosphorodichloridate (772-79-2) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8)

Conditions	Yield
Reaktion des Kaliumsalzes;

diethyl sulphite (623-81-4) + phosphorus pentachloride (10026-13-8, 874483-75-7) → thionyl chloride (7719-09-7) + chloroethane (75-00-3) + SO2

phosphorus pentachloride (10026-13-8, 874483-75-7) + 4,4'-sulfonyl-bis-benzenesulfonyl chloride (32337-45-4) → thionyl chloride (7719-09-7) + para-dichlorobenzene (106-46-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) + phosphorus trichloride (7719-12-2, 52843-90-0)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 1-Naphthalenesulfonyl chloride (85-46-1) → thionyl chloride (7719-09-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) + 1-Chloronaphthalene (90-13-1)

Conditions	Yield
at 150 - 160℃;

phenyltetrachlorophosphorane (4895-65-2) + sulfur dioxide → P,P-dichlorophenylphosphine oxide (824-72-6) + thionyl chloride (7719-09-7)

phenyl chlorosulphinate (13165-73-6) → thionyl chloride (7719-09-7) + diphenyl sulfite (4773-12-0)

Conditions	Yield
at 70℃; Einleiten von HCl;

phenyl chlorosulphinate (13165-73-6) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → thionyl chloride (7719-09-7) + phosphoric acid triphenyl ester (115-86-6)

2-benzoylamino-[1]naphthoic acid (861087-97-0) → thionyl chloride (7719-09-7) + 2-benzoyl-2H-naphth[2,1-b]azet-1-one

phosphorus pentachloride (10026-13-8, 874483-75-7) + 2,2'-sulfonyl-bis-benzenesulfonyl chloride → thionyl chloride (7719-09-7) + 1,2-dichloro-benzene (95-50-1)

Conditions	Yield
at 200 - 210℃;

tetrachloro-dipropylamino-phosphorane; compound with phosphorus pentachloride + SO2 → thionyl chloride (7719-09-7) + N,N-dipropylphosphoramidic dichloride (40881-98-9) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8)

phosphorus pentachloride (10026-13-8, 874483-75-7) + phenyl-methanesulfonic acid ; potassium salt → thionyl chloride (7719-09-7) + benzyl chloride (100-44-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8)

2',2',2'-Trichloroethyl 3-methyl-2-[2-chlorosulfinyl-4-oxo-3-(2-tert-butoxycarbonylamino-2-phenylacetamido)-1-azetidinyl]-3-butenoate → thionyl chloride (7719-09-7) + 2',2',2'-Trichloroethyl 3-methyl-2-[2-sulfino-4-oxo-3-(2-tert-butoxycarbonylamino-2-phenylacetamido)-1-azetidinyl]-3-butenoate

Conditions	Yield
In acetone

carbon disulfide (75-15-0) + hypochlorous anhydride (7791-21-1) → phosgene (75-44-5) + thionyl chloride (7719-09-7)

Conditions	Yield
In tetrachloromethane CS2 dild. in CCl4 (to diminuish vehemence of reaction);;
In tetrachloromethane

thionyl chloride (7719-09-7) + (S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloric acid salt → methyl (S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate hydrochloric acid salt (114786-39-9)

Conditions	Yield
In methanol for 3.5h; Heating / reflux;	100%

thionyl chloride (7719-09-7) + bis(tetrabutylammonium) hexatungstate → N(C4H9)4(1+)*WOCl5(1-) = [N(C4H9)4][WOCl5]

Conditions	Yield
In thionyl chloride (argon); stirring (ca. 16 h); pptn. with Et2O, washing (Et2O), drying (vac.);	100%

thionyl chloride (7719-09-7) + tetrabutylammonium decatungstate ammonium salt → N(C4H9)4(1+)*WOCl5(1-) = [N(C4H9)4][WOCl5]

Conditions	Yield
In thionyl chloride (argon); stirring (ca. 16 h); pptn. with Et2O, washing (Et2O), drying (vac.);	100%

thionyl chloride (7719-09-7) + (5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))V=O → (5,7,12,14-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinate(2-))VCl2 (173105-66-3)

Conditions	Yield
In dichloromethane (Ar); react. (0°C), warming (room temp.), stirring (6 h), solventevapn.; washing (diethyl ether, pentane), drying (high vacuum, 50°C, 8 h);	100%

thionyl chloride (7719-09-7) + Se4(1+)*[MoOCl4](1-)=Se4[MoOCl4] → [SeCl3][MoOCl4], β

Conditions	Yield
In thionyl chloride vac., 150°C, 3 d;	100%

thionyl chloride (7719-09-7) + 2-(2,6-dichlorophenyl)acetic acid (6575-24-2) → 1-bromo-3-(2,6-dichlorophenyl)propan-2-one (880089-70-3)

Conditions	Yield
Stage #1: thionyl chloride; 2-(2,6-dichlorophenyl)acetic acid With diazomethyl-trimethyl-silane Stage #2: With hydrogen bromide In water	100%

thionyl chloride (7719-09-7) + C14H12Cl2N2O3S (1218941-06-0) → C14H11Cl3N2O2S (1218941-07-1)

Conditions	Yield
	100%

thionyl chloride (7719-09-7) + 4-[1-(trifluoroacetyl)piperidin-4-yl]benzoic acid (1376437-09-0) → 4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzoyl chloride (1331747-36-4)

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 5h; Sealed tube;	100%

thionyl chloride (7719-09-7) + dimer acid (47818-40-6) → C36H62Cl2O2

Conditions	Yield
With triethylamine In ethyl acetate at 35℃; for 4h; Inert atmosphere;	100%

thionyl chloride (7719-09-7) + cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid → cobalt[2,9,16,23-tetrakis(chlorosulfonyl)]phthalocyanine

Conditions	Yield
at 80℃; for 12h;	100%

methanol (67-56-1) + thionyl chloride (7719-09-7) + 4-nitro-1H-pyrazole-3-carboxylic acid (5334-40-7) → methyl 4-nitro-1H-pyrazole-3-carboxylate (138786-86-4)

Conditions	Yield
at 0 - 25℃; for 16 - 48h; Product distribution / selectivity;	99.5%

silver(I) nitrite (7783-99-5) + thionyl chloride (7719-09-7) → nitrosylchloride (2696-92-6) + silver(I) chloride

Conditions	Yield
In diethyl ether byproducts: SO2; to finely ground dry Ag salt in anhyd. Et2O cooled to 0°C added dropwise with vigorous stirring equimolar amt. of thionyl chloride; suspn. stirred for 15 min; soln. was decanted from AgCl; AgCl dried; soln. washed (Et2O); all extracts combined; cooled to 0°C;	A n/a B 99%

thionyl chloride (7719-09-7) + silver nitrate → Nitryl chloride + nitrosylchloride (2696-92-6) + silver(I) chloride

Conditions	Yield
In diethyl ether byproducts: SO2, SO3; to finely ground dry Ag salt in anhyd. Et2O cooled to 0°C added dropwise with vigorous stirring equimolar amt. of thionyl chloride; suspn. stirred for 15 min; soln. was decanted from AgCl; AgCl dried; soln. washed (Et2O); all extracts combined; cooled to 0°C;	A n/a B n/a C 99%

thionyl chloride (7719-09-7) + (4,4'-dicarboxy-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride dihydrate → (4,4'-bis(chlorocarbonyl)-2,2'-bipyridine)bis(2,2'-bipyridine)ruthenium-(II) dichloride*SOCl2*HCl

Conditions	Yield
In dichloromethane (N2); stirring (4 h, reflux); solvent removal (reduced pressure), drying (vac., 60-70 degree.C, 1 h); elem. anal.;	99%

thionyl chloride (7719-09-7) + tributylammonium dodecaborododecahydride → 2(C4H9)3NH(1+)*B12H9(SO)3(2-)=((C4H9)3NH)2(B12H9(SO)3)

Conditions	Yield
In dichloromethane SOCl2 added to CH2Cl2 soln. of B compd. (molar ratio 1:3, 1:4); concd. slowly; ppt. purified by column chromy. (silica gel, CH2Cl2);	99%
In neat (no solvent) excess of SOCl2 added to B compd.; purified by column chromy. (silica gel, CH2Cl2);	99%
In dichloromethane SOCl2 added to CH2Cl2 soln. of B compd. (molar ratio 2:1, 1:1, 1:2); concd. slowly; mixt. of the starting B compd. and title compd. pptd.; purified by column chromy. (silica gel, CH2Cl2);	15%

thionyl chloride (7719-09-7) + [(C5(CH3)5)TiCl(C5H4C(CH3)2CH2CO2)] (864767-27-1) → [(C5(CH3)5)TiCl2(C5H4C(CH3)2CH2COCl)] (864767-39-5)

Conditions	Yield
In not given	99%

thionyl chloride (7719-09-7) + chloro(cyclopentadienyl)(cyclopentadienyl-3-methyl-3-butanoate)titanium(IV) (864766-99-4) → Cp(CpCMe2CH2COCl)titanium(IV)dichloride (864767-00-0)

Conditions	Yield
In not given	99%
In neat (no solvent) at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;

thionyl chloride (7719-09-7) + [(C5H5)TiCl(C5H4C(CH2)5CH2CO2)] (864767-24-8) → [(C5H5)TiCl2(C5H4C(CH2)5CH2COCl)] (864767-36-2)

Conditions	Yield
In not given	99%

thionyl chloride (7719-09-7) + chloro(cyclopentadienyl)(cyclopentadienyl-3-methyl-3-butanoate)titanium(IV) (864766-99-4) + cholesterol (57-88-5) → [(C5H5)TiCl2(C5H4C(CH3)2CH2CO2C27H45)]

Conditions	Yield
With sodium hydride In dichloromethane mixt. of Ti complex and SOCl2 was stirred for 3 h; evapd. (vac., 80°C); dissolved in CH2Cl2; added to mixt. of NaH and cholesterol; stirred for 16 h; filtered; solvent removed (vac.); crystd. (CH2Cl2);	99%

thionyl chloride (7719-09-7) + [(C5H5)TiCl(C5H4C(CH3)2CH2CH2CO2)] (1122084-99-4) + cholesterol (57-88-5) → [(C5H5)TiCl2(C5H4C(CH3)2(CH2)2CO2C27H45)]

Conditions	Yield
With sodium hydride In dichloromethane mixt. of Ti complex and SOCl2 was stirred for 3 h; evapd. (vac., 80°C); dissolved in CH2Cl2; added to mixt. of NaH and cholesterol; stirred for 16 h; filtered; solvent removed (vac.); crystd. (CH2Cl2);	99%

thionyl chloride (7719-09-7) + (4R,5S)-5-phenylthio-4-octanol (1202357-35-4) → ((4S,5R)-5-chlorooctan-4-yl)(phenyl)sulfane (1202357-36-5)

Conditions	Yield
With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; optical yield given as %ee;	99%

thionyl chloride (7719-09-7) + 1,7-dihydroxycarbonyl-1,7-dicarba-closo-dodecaborane (50571-15-8) → m-carborane-1,7-dicarboxylic acid dichloride (23810-52-8)

Conditions	Yield
In thionyl chloride B compd. and SOCl2 placed into a flask under N2, refluxed for 24 h; evapd. (vac.); obtained as an oil;	99%

thionyl chloride (7719-09-7) + tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl)methyl radical sodium salt (372515-55-4) → C40H36Cl3O3S12 (1079975-19-1)

Conditions	Yield
Stage #1: tris(8-carboxyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl)methyl radical sodium salt With triethylamine In chloroform at 20℃; for 0.5h; Stage #2: thionyl chloride In chloroform at 20 - 50℃;	99%

thionyl chloride (7719-09-7) + thallium chloride + chlorine (7782-50-5) → thallium (III) chloride (13453-32-2)

Conditions	Yield
In acetonitrile TlCl suspd. in CH3CN; Cl2 added under vigorous stirring; stirred for 30 min; soln. filtered; solvent evapd. in vacuum; SOCl2 added; evapd. after 10 min;	98.5%

thionyl chloride (7719-09-7) + tetrabenzyltin (10113-29-8) → phenylmethanesulfinyl chloride (41719-05-5) + dibenzyltin(IV) dichloride (3002-01-5)

Conditions	Yield
In not given dropwise addn. of thionyl chloride to tetraalkyltin(IV) compd. under dry N2 atmosphere under ice cooling, warming to room temp., refluxing for 30 min; distn. (removal of excess of SOCl2), cooling resulting liquids, sepn., elem. anal.;	A n/a B 98%

thionyl chloride (7719-09-7) + (29H,31H-2,9,16,23-tetracarboxyphthalocyaninato-N(29),N(30),N(31),N(32))cobalt(II) (69934-86-7) → cobalt tetra-4-(chlorocarbonyl)phthalocyanine (73533-44-5)

Conditions	Yield
In benzene a mixt. in dry benzene was refluxed for 7 h; filtered, washed with dry benzene, dried in a vac. at room temp.;	98%
With pyridine In benzene at 80℃;	96%

thionyl chloride (7719-09-7) + 2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylic acid (72850-61-4) → 2-chloro-4-(trifluoromethyl)-5-thiazolecarbonyl chloride (72850-62-5)

Conditions	Yield
6 h refluxing with excess SOCl2;	98%

thionyl chloride (7719-09-7) + (m-carborane-9,10-diyl)diacetic acids (683816-30-0) → (m-carboranyl-9,10-diyl)di(acetyl chlorides) (683816-32-2)

Conditions	Yield
In benzene byproducts: SO2, HCl; addn. of SOCl2 to soln. of (CH2COOH)2C2B10H10 in dry benzene at 20°C; heating for 2 h; cooling, removal of solvent and excess SOCl2 in vac.;	98%

thionyl chloride (7719-09-7) + C6H3F2N2(1+)*Cl(1-) (1489175-55-4) → 2,3-difluorobenzenesulphonyl chloride (210532-24-4)

Conditions	Yield
Stage #1: thionyl chloride With copper(l) chloride In water at -5 - 20℃; Stage #2: C6H3F2N2(1+)*Cl(1-) In water at -5℃; for 0.5h;	98%

Upstream product

• 56-23-5 tetrachloromethane 
• 7446-70-0 aluminium trichloride 
• 75-15-0 carbon disulfide 
• 67-66-3 chloroform 
• 10025-67-9 disulfur dichloride 
• 7790-94-5 chlorosulfonic acid 
• 10545-99-0 sulfur dichloride 
• 7782-50-5 chlorine 
• 7664-93-9 sulfuric acid 
• 1313-82-2 sodium sulfide 
• 7791-21-1 hypochlorous anhydride 
• 14177-25-4 thionyl chlorofluoride 
• 74354-27-1 S₈OSbCl₅ 
• 75-44-5 phosgene 

Downstream Products

• 15118-67-9 ethyl 3-(4-methoxybenzoyl)-propionate 
• 5205-39-0 ethyl glutaroyl chloride 
• 1071-71-2 ethyl 6-chloro-6-oxohexanoate 
• 125452-97-3 2-(1'-Methylvinyl)-2-phenylpropane-1,3-diol Sulfite 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 98138-06-8 4,6-dichloro-pyridine-2-carbonyl chloride 
• 71022-75-8 4-chloropyridine-2,6-dicarbonyl dichloride 
• 138813-24-8 4H,9H-Dipyrazolo<1,5-a:1',5'-d>pyrazin-4,9-dion 
• 861621-72-9 3-chloro-4-methoxy-4-phenyl-chroman 
• 110-56-5 1,4-dichlorobutane 
• 625-36-5 2-chloropropionyl chloride 
• 447-31-4 Desyl chloride 
• 134-81-6 benzil 
• 7299-58-3 phenylpropiolyl chloride 

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